반응 #81558

반응 방정식

Methyl 1,1-dimethyl-3-(trifluoromethanesulfonyloxy)-1H-indene-5-carboxylate

lithium chloride

phenyltributyltin

→

title compound

수율 83.1%

Methyl 1,1-dimethyl-3-phenyl-1H-indene-5-carboxylate

수율 83.1%

용매

—

2-methyl pyrrolidinone

water

반응 조건

후처리

1. 1
   추출extracted with ethyl ether (30 mL×3)
2. 2
   건조The combined extracts were dried over magnesium sulfate
3. 3
   기타evaporated
4. 4
   기타The residue was purified by flash chromatography (EtOAc:hexane=1:20 to 1:5)

실험 절차

Methyl 1,1-dimethyl-3-(trifluoromethanesulfonyloxy)-1H-indene-5-carboxylate (580 mg, 1.86 mmol ), tris(dibenzylideneacetone)dipalladium (0) (Pd2 dba3, 17 mg, 0.02 mmol), triphenylarsine (46 mg, 0.15 mmol), lithium chloride (240 mg, 5.59 mmol) and phenyltributyltin (680 mg, 1.86 mmol) in 5 mL of 2-methyl pyrrolidinone were stirred at 55° C. for 1.5 days. The mixture was diluted with water (30 mL), and extracted with ethyl ether (30 mL×3). The combined extracts were dried over magnesium sulfate and evaporated. The residue was purified by flash chromatography (EtOAc:hexane=1:20 to 1:5) to give 0.43 g (83% yield) of the title compound as a white solid; 1H-NMR (CDCl3) δ1.41 (s, 6H), 3.91 (s, 3H), 6.48 (s, 1H), 7.39-7.62 (m, 6H), 7.99 (d, J=6.8 Hz, 1H), 8.14 (s, 1H); MS m/e 279 (MH+).

출처